WiscoREIA Sheboygan Falls: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (19 Aug 2026)

Wed, 19 Aug 2026 22:30:00 GMT

STR Guest Experience Masterclass:

Turn Every Stay into a 5-Star Story

Want to stand out in a saturated short-term rental market?

It’s not just about the property, it’s about the experience.

Join seasoned STR investor Ashley Lang (29 units and counting) for a no-fluff, real-talk presentation on delivering 5-star guest experiences that actually grow your business.

We’re talking:

✔️ How to create wow-factor moments without blowing your budget

✔️ Messaging strategies that prevent problems before they start

✔️ Handling guest drama like a pro (yes, even those guests)

✔️ Systems that make 5-star reviews the norm

✔️ The secret to turning one-time guests into loyal repeat bookers

✔️ How scale your STR portfolio

Whether you’re managing your first unit or scaling a portfolio, this session will give you tangible tools to elevate your guest experience, and your bottom line.

Speaker: Ashley Lang

Ashley Lang is a powerhouse real estate investor, short-term rental expert, and the founder of Clear Trail Properties. Since entering the short-term rental space in 2018, Ashley has built and scaled a high-performing STR portfolio rooted in one core belief: great design and great systems create great returns.

She currently owns and operates 25+ short-term rental units across Arizona, Central Wisconsin, Northern Wisconsin, and Michigan’s Upper Peninsula, while also scaling a rapidly growing co-hosting company managing an additional 20+ units across the same markets. In addition, Ashley oversees 25+ long-term rentals and flips single-family homes alongside her partner, Buck.

Ashley is known for her obsession with intentional STR design—from floor plans and furniture layouts to guest flow, durability, and the smallest finishing details. She believes design is not decoration; it’s a strategic tool that directly impacts occupancy, ADR, guest experience, and long-term asset performance. Her approach blends creativity with operational efficiency, ensuring properties are not only beautiful, but profitable and scalable.

Beyond building her own real estate empire, Ashley is passionate about teaching and coaching other investors to shorten their learning curve, avoid costly mistakes, and create freedom through real estate-backed businesses. Her work empowers others to confidently turn a vision into a high-performing short-term rental operation.

When she’s not running her companies, Ashley enjoys mountain biking, hiking, camping, and traveling with her boyfriend Buck, their son Korbin, and their four beloved bulldogs.

WiscoREIA Sheboygan Falls' Meeting Always Meets on the 3rd Wednesday of the Month from

5:30 pm to 8:15 pm!

Host: Kyle Kaufman

Kyle Kaufman is a law firm owner, attorney, real estate investor, and host of the Meaningful Ideas Trading Club. Kyle was born and raised in Wisconsin. He grew up wanting to help people. He has discovered his life’s purpose to help families in Wisconsin and to provide individuals with commercial space for their business, and residences for people to live.

In 2005 Kyle started practicing law. He handled almost all aspects of the law. Early in his career he took on landlord and tenant matters, and civil disputes involving real estate. He started to advise people starting their real estate portfolios, and drafted documents for investors to use in their businesses and with tenants and property managers.

In 2010 Kyle became a one-third owner of the law firm, now known as HKK Law Offices (www.hkklawoffices.com). Kyle’s practice shifted to family law sometime around 2018, as more and more people called seeking his assistance. Kyle became fascinated with the financial information he discovered while representing individuals in divorce matters and financial disputes between former significant others. He started to study more thoroughly on the issues of real estate, business, taxes, and more.

Today, Kyle’s law practice focuses entirely on family law, including divorce, maintenance, child support, paternity, property division, child custody, adoption, termination of parental rights, guardianship and more. In the legal world, he sees his contributions in this area to have the most transformational impact on the community. An associate at his law firm practices estate planning.

Kyle now owns one-half of the law firm business and leads a team of 15 people.

Real estate has always been an interest, and after advising clients for many years, Kyle and his wife, Sunny, decided to join in on the fun. In the year 2020, Kyle and Sunny purchased a building with 18 residential units and two commercial units. In 2021, with a partner, they purchased two commercial properties. In 2022, Kyle and Sunny bought a 44,000 square foot warehouse with 3 parking lots. They sold the warehouse in 2025 for a profit. In 2025, they converted their Chicago condo into a rental unit, and then acquired 3 duplexes. They are generating passive income from their investments and using the power of delegation to make it all work.

In 2021 Kyle created an online weekly meetup event called the Meaningful Ideas Trading Club. Kyle hosts the program and invites others to share and mastermind on ideas related to personal and business development.

Outside of business, Kyle and Sunny have 6 children, and they enjoy spending their time with their family.

Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!

Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!

Our Agenda

5:30 PM – Registration Check-In & Networking

• Informal networking with fellow investors

6:00 PM – Meeting Kickoff

• Welcome by Host and/or Co-Host

• WiscoREIA PowerPoint / announcements and updates

• Sponsor Introductions

• Haves & Wants – Share deals, services, and resources

6:30 PM – Deal Case Study

• Breakdown of a real deal with teachable moments (good, bad, ugly)

7:00 PM – Networking Breakouts

• Guest Orientation with Host

• Member & Sponsor general breakout for continued connection

7:15 PM – Main Presentation

• Host introduces Guest Speaker

8:15 PM – Closing Remarks

• Final thoughts and upcoming events

• Invitation to the "Meeting After the Meeting" for more networking

The meeting ends at 8:15 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.

You can stay after the meeting as well to network! Remember to bring your deals!

Our doors are open to EVERYONE!

***Make sure to pre-register***

Click here to pre-register!

WiscoREIA upcoming events

WiscoREIA Sheboygan Falls: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (19 Aug 2026)